Brompheniramine

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Brompheniramine
Clinical data
Trade namesBromfed, Dimetapp, Bromfenex, others
AHFS/Drugs.comMonograph
MedlinePlusa682545
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • AU: S4 / S3 / S2
  • US: Rx-only / OTC
Pharmacokinetic data
MetabolismLiver
Elimination half-life24.9 ± 9.3 hours[1]
ExcretionKidney
Identifiers
  • (R/S)-3-(4-Bromophenyl)-N,N-dimethyl-3-pyridin-2-yl-propan-1-amine
JSmol)
  • Brc1ccc(cc1)C(c2ncccc2)CCN(C)C
  • InChI=1S/C16H19BrN2/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h3-9,11,15H,10,12H2,1-2H3 checkY
  • Key:ZDIGNSYAACHWNL-UHFFFAOYSA-N checkY
  (verify)

Brompheniramine, sold under the brand name Dimetapp among others, is a first-generation antihistamine drug of the propylamine (alkylamine) class.[2] It is indicated for the treatment of the symptoms of the common cold and allergic rhinitis, such as runny nose, itchy eyes, watery eyes, and sneezing. Like the other first-generation drugs of its class, it is considered a sedating antihistamine.[2]

It was patented in 1948 and came into medical use in 1955.[3] In 2021, the combination with dextromethorphan and pseudoephedrine was the 294th most commonly prescribed medication in the United States with more than 500,000 prescriptions.[4][5]

Side effects

Brompheniramine's effects on the cholinergic system may include side-effects such as drowsiness, sedation, dry mouth, dry throat, blurred vision, and increased heart rate. It is listed as one of the drugs of highest anticholinergic activity in a study of anticholinergenic burden, including long-term cognitive impairment.[6]

Pharmacology

Brompheniramine works by acting as an

antimuscarinic agent similar to other common antihistamines such as diphenhydramine
.

Brompheniramine is metabolised by

isoenzymes
in the liver.

Chemistry

Brompheniramine is part of a series of antihistamines including

optical isomerism; brompheniramine products contain racemic brompheniramine maleate, whereas dexbrompheniramine (Drixoral) is the dextrorotary (right-handed) stereoisomer.[2][7]

Brompheniramine is an

chlorpheniramine. The only difference is that the chlorine atom in the benzene ring is replaced with a bromine atom. It is also synthesized in an analogous manner.[8][9]

History

Arvid Carlsson and his colleagues, working at the Swedish company Astra AB, were able to derive the first marketed selective serotonin reuptake inhibitor, zimelidine, from brompheniramine.[10]

Names

Brand names include Bromfed, Dimetapp, Bromfenex, Dimetane, and Lodrane. All bromphemiramine preparations are marketed as the

maleate salt.[2]

References

  1. PMID 6128358
    .
  2. ^
    OCLC 56903116
    .
  3. ISBN 9783527607495
    .
  4. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  5. ^ "Brompheniramine; Dextromethorphan; Pseudoephedrine - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  6. PMID 25879993
    .
  7. ISBN 9780781746731
    .
  8. ^ US 3061517, Walter LA, issued 1962. 
  9. ^ US 3030371, Walter LA, issued 1962. 
  10. ISBN 0-19-515130-5
    .
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